This reply is a little tardy but I'm new to this forum.
We just bought a pair of Sports, an '08 at a sale price and an '09. My main concern was not having to support two incompatible sets of spare parts. The dealer pointed out, however, that this '08 had the same V2 drive as the '09, some do. You might check into that.
As for the other differences I am too inexperienced to trust too much but my initial observations are: Both rudder setups have small advantages. The '08 is inclined to stay up when transporting but that sometimes gets in the way when rigging a stern tie down. The '09 can be easily moved to rig the tie down but sometimes comes down when it should be up. Hobie moved the bungees aft a few inches on the '09 to help with this. In the water they retract differently but both seem to work fine. The '09 might have some advantage in kicking up if it isn't locked down but I haven't tested this.
The '09 drive latches are certainly snazzier but the '08 latches seem to work fine. They are simpler, and may be a bit easier to install the drive (or it could just be we haven't yet learned the knack of doing this well). The '08 latches look like they may be more inclined to come loose but have shown no inclination to do so yet.
Hope this is some help.
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